1,2-Dichloroethane → HCID 18758332, compound

HRID 1661782Notes

Reaction equation

HRID 1661782 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([N:20]3[C:28](=[O:29])[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]=4[NH2:30])C3=O)[CH2:16][C:17](=[O:19])[CH3:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:32]OC1CCC(OC)O1.[C:41]([OH:44])(=O)[CH3:42].Cl[CH2:46][CH2:47]Cl>C(Cl)Cl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([N:20]3[C:41](=[O:44])[C:42]4[C:27](=[CH:22][CH:23]=[CH:24][C:25]=4[C:26]4[NH:30][CH:32]=[CH:46][CH:47]=4)[C:28]3=[O:29])[CH2:16][C:17](=[O:19])[CH3:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 790982,5-DimethoxytetrahydrofuranHCID 18758339HCID 18758339, compound

Product 1

HCID 18758332HCID 18758332, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-3-oxobutyl]-4-aminoisoindoline-1,3-dione (0.41 g, 0.97 mmol), 2,5-dimethoxytetrahydrofuran (0.14 g, 1.07 mmol) and acetic acid (2 mL) in 1,2-dichloroethane (10 mL) was refluxed for 1 hour. The mixture was diluted with methylene chloride (25 mL) and washed with water (2×20 mL), brine (20 mL) and dried. Solvent was removed and the residue was purified by chromatography (Silica gel, Hexane:ethyl acetate 6:4) to give 2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-3-oxobutyl]-4-pyrrolylisoindoline-1,3-dione (0.41 g, 91%) as a white solid: mp 142-144° C.; 1H NMR (CDCl3) δ 7.72-7.56 (m, 3H), 7.14-7.04 (m, 4H), 6.79 (d, J=8.2 Hz, 1H), 6.38 (m, 2H), 5.77-5.71 (dd, J=5.4, 9.8 Hz, 1H), 4.77 (m, 1H), 4.05-3.94 (dd, J=9.9, 18.9 Hz, 1H), 3.79 (s, 3H), 3.30-3.21 (dd, J=5.4, 18.0 Hz, 1H), 2.16 (s, 3H), 1.98-1.60 (m, 8H); 13C NMR (CDCl3) δ 205.31, 167.21, 166.14, 149.75, 147.61, 138.35, 135.09, 133.98, 131.34, 129.91, 126.04, 121.31, 120.74, 120.20, 114.72, 111.68, 110.61, 80.38, 55.97, 50.18, 44.72, 32.74, 30.12, 24.03; Anal. Calcd. for C28H28N2O5; C, 71.17; H, 5.97; N, 5.93. Found: C, 71.09; H, 6.09; N, 5.80.

Workup

  1. temperaturewas refluxed for 1 hour
  2. washwashed with water (2×20 mL), brine (20 mL)
  3. customdried
  4. customSolvent was removed
  5. customthe residue was purified by chromatography (Silica gel, Hexane:ethyl acetate 6:4)

Sources & evidence

ORD record
ord-d18d17d776344cf09f82df3756da52b8
Source dataset
uspto-grants-2011_10
Patent number
US08030343B2

Reaction notes

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